Plastic lens and method production thereof

ABSTRACT

The present invention includes a plastic lens having a plastic lens base material, a primer layer formed on the plastic lens base material, and a hard coat layer formed on the primer layer, the hard coat layer being formed from a hard coat composition having (A) an inorganic fine particle having a particle diameter of 1 to 100 millimicrons, (B) an organic silicon compound expressed in terms of a specified Formula (1), (C) a multi-functional epoxy compound, and (D) a curing catalyst. Such a plastic lens is excellent in shock impact resistance by including the primer layer and also shows improvements in scratch resistance, water resistance, and permanence properties while keeping the coloring properties of the hard coat layer of a colorable type.

TECHNICAL FIELD

The present invention relates to a plastic lens, particularly to aplastic lens that has a hard coat layer capable of being colored andthat is also excellent in shock impact resistance and to themanufacturing method thereof.

BACKGROUND ART

Plastic lenses are widely used in the field of spectacle lenses due tolightweight, good formability, good processability, and good coloringproperties as well as being hard-to break and also highly safety, ascompared with glass lenses.

Plastic lenses, however, are soft and very easy to scratch, and thus arebeing improved in scratch resistance by applying a hard coat layer withhigh hardness to the surface of a plastic lens. Further, for the purposeof preventing surface reflection, an anti-reflection coating on whichinorganic material is vacuum deposited is also put on the surface of ahard coat layer in some cases. Because of such a surface-treating layerfor a plastic lens, the quality of a plastic lens is high.

Nonetheless, a plastic lens subjected to surface treatment with a hardcoat layer or an anti-reflection coating has the disadvantage of shockimpact resistance being lowered, as compared to a plastic lens havingabsolutely no surface treating layer. In particular, a lens with a minuspower lens, i.e., the center of the lens being thin, is extremelydecreased in shock impact resistance leading to the disadvantage ofbeing easily broken. When the thickness of the center is made large toimprove the disadvantage, the thickness of the peripheral portion (edgethickness) of the lens is very large, and so the appearance is notpreferable. Also, the weight of the lens becomes large, and a feel ofusing the glasses is lowered so that the practically is not preferable.In recent years, the development of plastic lens base materials withlarge refractive indexes have progressed, which can make small thecenter and edge thickness of a lens; however, a plastic base materialwith a large index of refraction has disadvantages of shock impactresistance being low and of being easily broken.

In order to dissolve these problems, placing a primer layer between theplastic lens material and the hard coat layer is proposed. Originally,the primer layer is a layer for improving adhesion properties betweenthe plastic lens base material and the hard coat layer, but the shockimpact resistance of the plastic lens can be improved by selecting aspecific resin as the primer layer.

Related art documents of these primer layers include, for example,Japanese Patent Laid-open Nos. Sho 61-114203, Sho 63-87223, Sho63-141001, Hei 3-109502, and 2000-144048.

In addition, hard coat layers are divided into a colorable type capableof coloring and a non-colorable type incapable of coloring. A colorabletype hard coat layer has the advantage of freely coloring a plastic lensby coloring the hard coat layer according to a purchaser's desire afterthe finished plastic lens without coloring is supplied to a purchaser.

For that reason, some purchasers are requesting plastic lenses having ahard coat layer of a colorable type. In addition to this, the plasticlens is desired to be excellent in shock impact resistance.

As such, plastic lenses that have a hard coat layer of a colorable typeand that are excellent in shock impact resistance are required on themarket.

However, a plastic lens having coloring properties and offering animprovement in shock impact resistance by placing the above-describedprimer layer between the plastic lens base material and the hard coatlayer of a colorable type has the following disadvantages.

First, a hard coat layer of a colorable type poses problems of thehardness being low and of the scratch resistance being inferior to thatof a hard coat layer of a non-coloring type, due to containing coloringcomponents. Making small the amount of blending of coloring componentsincreases the hardness, whereas the coloring properties become poor.

In addition, a hard coat layer when being colored is sometimes immersedin a high-temperature coloring solution. On this occasion, there is aproblem of cracks occurring for the hard coat layer poor in waterresistance and in hot water resistance.

Furthermore, the adhesion properties between the primer layer and thehard coat layer and further the adhesion properties between the hardcoat layer and the anti-reflection coating are insufficient; as aresult, these cause a problem of the permanence properties of theplastic lens being inferior.

The present invention is made taking into account the above-describedsituations, and the object thereof is to provide a plastic lens havingexcellent shock impact resistance by introducing a primer layer andimproving scratch resistance, water resistance, and permanenceproperties while maintaining the coloring properties of a hard coatlayer of a colorable type.

Moreover, the present invention is directed to the provision of a methodfor manufacturing a plastic lens, which enables the production of such aplastic lens.

DISCLOSURE OF INVENTION

The present inventor, as a result of earnest studies to attain theabove-described object, has found out that in a plastic lens having aprimer layer formed on a plastic lens base material and having a hardcoat layer formed on the primer layer, it is effective for the hard coatlayer to be formed by making use of a hard coat composition containingan inorganic fine particle, an organic silicon compound as a vehicle, amulti-functional epoxy compound as a coloring component and a curingcatalyst.

In other words, the coloring properties of a hard coat layer of acolorable type become much higher in the case where the hard coat layeris formed on the plastic lens base material via a primer layer than thecase where the hard coat layer of a colorable type is singly layered onthe plastic lens base material. For that reason, placing of a primerlayer allows a coloring component in a hard coat layer of a colorabletype to be reduced, thereby obtaining, in addition to ensure sufficientcoloring properties, a plastic lens with higher hardness and thusimproved scratch resistance. In this case, sufficient coloringproperties can be obtained, with the content of a multi-functional epoxycompound in the solid matter of the hard coat composition being in therange of from 0.1 to 25% by weight.

A multi-functional epoxy compound as a coloring component enables theimprovement of water resistance and hot water resistance of a hard coatlayer and thus can effectively suppress the generation of cracks duringcoloring.

In addition, a hard coat layer blended with a multi-functional epoxycompound is particularly excellent in adhesion properties with a primerlayer containing as the main component a water borne acryl/urethaneresin or as the main component a polyester-based thermoplasticelastomer, and therefore can produce a plastic lens excellent inpermanence properties. Furthermore, the presence of the hydroxyl groupin a molecule of a multi-functional epoxy compound improves adhesionproperties with a primer layer and coloring properties. Thus, the use ofa multi-functional epoxy compound containing one or more hydroxyl groupsper molecule enables the further reduction of the amount of blending ofthis multi-functional epoxy compound, and thus can further improve thescratch resistance. Moreover, a hard coat layer containing amulti-functional epoxy compound can improve the shock impact resistanceof the plastic lens.

A primer layer containing as the main component a water borneacryl/urethane resin or as the main component a polyester-basedthermoplastic elastomer can provide the plastic lens with excellentshock impact resistance as well as being good in water resistance andweather resistance. Also, the primer layer is exceptionally good inadhesion properties with the hard coat layer containing amulti-functional epoxy compound.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, embodiments of a plastic lens of the present invention andthe manufacturing method thereof will be set forth; however, the presentinvention is by no means limited to the following embodiments.

A plastic lens of the present invention, as described above, has astructure having a primer layer formed on a plastic lens base materialand having a hard coat layer of a colorable type formed on the primerlayer.

Plastic lens base materials are not particularly limited and theillustrative examples can include styrene resin, polycarbonate resin,allyl resin, allyl carbonate resin such as diethylene glycol-bisallylcarbonate resin (CR-39) as well as methacrylic resin, vinyl resin,polyester resin, polyether resin, urethane resin obtained by reacting anisocyanate compound with a hydroxyl compound such as diethylene glycol,thiourethane resin obtained by reacting an isocyanate compound with apolythiol compound, transparent resin obtained by curing a polymerizedcompound containing a thioepoxy compound having one or more disulfidesin the molecule.

A primer layer is preferably water borne acryl/urethane resin or apolyester-based thermoplastic elastomer, which significantly improvesthe shock impact resistance of a plastic lens and which is excellent inwater resistance and light resistance as well as being excellent inadhesion properties with the hard coat layer of a colorable type, asdiscussed below.

Water borne acryl/urethane resin, which is dispersed in water, refers toa copolymer between an acrylic polyol and a multi-functional isocyanatecompound, or a complex between an acrylic polyol and water bornepolyurethane resin.

An acrylic polyol stands for copolymer acrylic resin between an acrylmonomer having a hydroxyl group and a monomer such as an acryl estercapable of being copolymerized with the acryl monomer having a hydroxylgroup. Water borne polyurethane resin is also called water borneurethane resin or a water dispersion type polyurethane, and refers toresin in which urethane resin obtained by reacting a multi-functionalisocyanate compound with a polyol is dispersed in water as an emulsion.

Acryl monomers having a hydroxyl group, which are raw material of anacrylic polyol, include 2-hydroxyethyl acrylate, 3-chloro-2-hydroxybutylacrylate, 2-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate,2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate,6-hydroxyhexyl methacrylate, and 5,6-dihydroxyhexyl methacrylate. Thesemay be used solely or in a combination of two or more species.

In addition, examples of monomers capable of being copolymerized with anacryl monomer having a hydroxyl group include methyl (metha)crylate,ethyl (metha)crylate, n-propyl (metha)crylate, n-butyl (metha)crylate,isopropyl (metha)crylate, isobutyl (metha)crylate, n-amyl(metha)crylate, n-hexyl (metha)crylate, isoamyl (metha)crylate,trifluoroethyl (metha)crylate, benzyl (metha)crylate, 2-n-butoxyethyl(metha)crylate, 2-chloroethyl (metha)crylate, sec-butyl (metha)crylate,tert-butyl (metha)crylate, 2-ethylbutyl (metha)crylate, cinnamyl(metha)crylate, cyclohexyl (metha)crylate, cyclopentyl (metha)crylate,2-ethoxyethyl (metha)crylate, furfuryl (metha)crylate,hexafluoroisopropyl (metha)crylate, 3-methoxybutyl (metha)crylate,2-methoxybutyl (metha)crylate, 2-nitro-2-methylpropyl (metha)crylate,n-octyl (metha)crylate, 2-ethylhexyl (metha)crylate, 2-phenoxyethyl(metha)crylate, 2-phenylethyl (metha)crylate, phenyl (metha)crylate,tetrahydrofurfuryl (metha)crylate, tetrapyranyl (metha)crylate,acryl-based monomers such as acrylic acid and methacrylic acid, andfurther ethylene-based monomers such as acrylonitrile, vinyl acetate,vinylpyridine, vinylpyrrolidone, methyl crotonate, maleic anhydride,styrene, and α-methylstyrene. Additionally, (metha)crylate refers toacrylate or methacrylate.

An acrylic polyol can be obtained by polymerizing an acryl monomerhaving the hydroxyl group thereof with a monomer capable of beingcopolymerized therewith by means of the well-known polymerizing processsuch as the bulk polymerizing process, the solution polymerizingprocess, or the emulsification polymerizing process. In particular, theemulsification polymerizing process is preferable in that a largemolecular weight polymer, which is difficult to produce by solutionpolymerization, is obtainable, in addition to directly producing a waterborne acrylic polyol.

In addition, in order to obtain water borne polyurethane resin of aself-emulsifiable type, together with an acrylic polyol, a compoundhaving a carboxyl group and at least two active hydrogen atoms in themolecule is preferably used. These compounds include, for example,2,2-dimethylol propionic acid, 2,2-dimethylol butyric acid,2,2-dimethylol valeric acid, dioxymaleic acid, and 2,2-dimethylolbutanoic acid. These compounds may be used solely or in a combination oftwo or more species.

On the other hand, multi-functional isocyanate compounds includediisocyanates such as toluene diisocyanate, diphenylmethanediisocyanate, 3,3′-dimethyl-4,4′-diphenylene diisocyanate,1,5-naphtalene diisocyanate, tolidine diisocyanate, hexamethylenediisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate,norborane diisocyanate, p-phenylene diisocyanate,t-cyclohexane-1,4-diisocyanate, xylene diisocyanate, water-added xylenediisocyanate, water-added diphenylmethane diisocyanate, lysinediisocyanate, tetramethylxylene diisocyanate, trimethylhexamethylenediisocyanate, and 1,3-bis(isocyanatemethyl) cyclohexane; andtriisocyanates such as triphenylmethane triisocyanate,tris(isocyanatephenyl) thiophosphate, lysine ester triisocyanate,2-isocyanateethyl-2,6-diisocyanate hexanoate, 1,6,11-undecanetriisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane,1,3,6-hexametylene triisocyanate, and bicycloheptane triisocyanate.Moreover, urethane modified species obtained from these diisocyanatesand triisocyanates are usable. Urethane modified species include adductspecies, urethidione species (dimer), isocyanurate species (trimer),carbodiimide, allophanate modified species, urea modifiedpolyisocyanates, buret modified polyisocyanates, and isocyanateprepolymers (semiprepolymers). Furthermore, urethane modified speciesinclude block isocyanates prepared by blocking polyisocyanates withblocking agents such as acetylacetone, dimethylmalonate,diethylmalonate, 2,4-hexanedione, 3,5-heptanedione, acetoxime,methylethylketoxime, pucnoneoxime, and caprolactam.

Of these, aliphatic diisocyanate compounds and alicyclic diisocyanatesare preferable from the viewpoint of weather resistance, and, forexample, isophorone diisocyanate, dicyclohexylmethane diisocyanate,norborane diisocyanate, and hexamethylene diisocyanate are preferable.

There is a method for obtaining water borne acryl/urethane resin thatinvolves, for example, reacting an acrylic polyol, as appropriate,another polyol, the aforementioned compound having a carboxyl group andat least two active hydrogen atoms, a multi-functional isocyanatecompound, which is stoichiometrically excessive relative to the hydroxylgroup, and a catalyst in an organic solvent to produce an acryl modifiedurethane prepolymer having a carboxyl group and having an isocyanategroup at a terminal, neutralizing the resultant solution with aneutralizing agent to make the material water borne, dispersing thiswater borne urethane prepolymer in water, and further polymerizing theprepolymer with a chain-extending agent to obtain a water borneacryl/urethane copolymer composition of a self-emulsifiable type.

Polyols other than acrylic polyols include, for example, polyester-basedpolyols, polycarbonate-based polyols, and polyether-based polyols. Thesepolyols can be used solely or in a combination of two or more species.

Polyester-based polyols include, for example, polyethylene adipate,polyethylene propylene adipate, polybutylene adipate, polyethylenebutylene adipate, polyhexamethylene adipate, polydiethylene adipate,polyethylene terephthalate, polyhexamethylene isophthalate adipate,polyethylene succinate, polybutylene succinate, polyethylene sebacate,polybutylene sebacate, poly-ε-caprolactonediol,poly-3-methyl-1,5-pentylene adipate, or polyester polyols having aterminal hydroxyl group produced from polycondensation compounds or thelike between 1,6-hexanediol and a dimer acid.

In addition, polycarbonate-based polyols can include, for example,polyhexamethylene carbonate diol.

Furthermore, polyether-based polyols include, for example, homopolymers,block copolymers, and random copolymers of polyethylene glycol,polypropylene glycol, polytetramethylene glycol, and the like.

The aforementioned catalysts include dimethyltin dilaurate, stannousoctoate, dibutyltin-2-ethylhexoate, triethylamine, triethylenediamine,and N-methylmorpholine. One or two or more species of these can be used.

Moreover, examples of neutralizing agents include amines such astrimethylamine, triethylamine, tri-n-propylamine, tributylamine, andtriethanolamine, potassium hydroxide, sodium hydroxide, and ammonia.

Additionally, examples of chain extending agents include low molecularweight multi-functional alcohols such as ethylene glycol,1,4-butanediol, 1,6-hexanediol, trimethylolpropane, pentaerythritol, andsorbitol, and further low molecular weight polyamines such asethylenediamine, propylenediamine, hexamethylenediamine,diaminocyclohexylmethane, piperazine, 2-methylpiperazine,isophoronediamine, diethylenetriamine, and triethylenetetramine. Thesecan be used singly or in a combination of two or more species.

In the case of the amount of blending of compound having a carboxylgroup and at least two active hydrogen atoms, the content of carboxylgroups in the resin is preferably from 0.3 to 5% by weight, particularlypreferably from 0.5 to 1.5% by weight.

Illustrative examples of commercialized products of water borneacryl/urethane resin of a self-emulsifiable type can include Neosticker400, Neosticker 700, and X-7200 (trade name; all the products from NiccaChemical Co., Ltd.). This water dispersion type polyurethane undergoes afurther improvement in water resistance by adding a crosslinking agentthat reacts with the carboxyl group such as an aqueous oxazoline-basedcrosslinking agent, an aqueous (poly) carbodiimide-based crosslinkingagent, or an aqueous epoxy resin-based crosslinking agent.

In addition, a method that does not use a compound having a carboxylgroup and at least two active hydrogen atoms is present. The methodentails reacting an acrylic polyol, as appropriate, another polyol, amulti-functional isocyanate compound, which is stoichiometricallyexcessive relative to the hydroxyl group, and a catalyst in an organicsolvent to produce an acryl modified urethane prepolymer having anisocyanate group at a terminal, dispersing this urethane prepolymer inwater with a surfactant, and further polymerizing the prepolymer with achain-extending agent to obtain a water borne acryl/urethane copolymercomposition of a forced emulsifiable type.

Furthermore, another method obtaining water borne acryl/urethane resinis present. The method involves reacting an acrylic polyol containing inthe above-mentioned ratio the aforementioned compound having a carboxylgroup and having at least two active hydrogen atoms with amulti-functional isocyanate compound in a equivalent ratio of theisocyanate group to the active hydrogen group being from 0.8:1 to 1.2:1,neutralizing the carboxyl groups with the above-described neutralizingagent and subsequently water dispersing the polyurethane.

Additionally, a method without using a compound having a carboxyl groupand having at least two active hydrogen atoms exists. The methodincludes reacting an acrylic polyol with a multi-functional isocyanatecompound in a equivalent ratio of the isocyanate group to the activehydrogen group being from 0.8:1 to 1.2:1, and then dispersing theresultant polyurethane resin in water using a surfactant to yield waterborne acryl/urethane resin.

Still additionally, there is a method involving, for example, emulsionpolymerizing an acryl monomer in the presence of water bornepolyurethane resin to obtain a complex emulsion, which is a complexhaving a core shell structure between an acrylic polyol and water bornepolyurethane resin.

This method includes, for example, reacting an acrylic polyol containingin the above-mentioned ratio the aforementioned compound having acarboxyl group and having at least two active hydrogen atoms with amulti-functional isocyanate compound in a equivalent ratio of theisocyanate group to the active hydrogen group being from 0.8:1 to 1.2:1,neutralizing the carboxyl groups with the above-described neutralizingagent, and subsequently water dispersing the polyurethane. In thewater-based medium in the presence of this water dispersed polyurethaneis placed an acryl monomer and the resulting mixture is polymerized witha polymerization initiator to be capable of obtaining water borneacryl/urethane resin having a core shell structure.

Furthermore, water borne acryl/urethane resin can be obtained as well bysimply blending water borne polyurethane resin with an acrylic polyolemulsion obtained by the emulsification polymerizing process.

Because the refractive index of water borne acryl/urethane resin isabout 1.5, due to recently making larger the refractive index of aplastic lens base material, applying directly water borne acryl/urethaneresin as a primer layer on a plastic lens base material having arefractive index of about 1.7 produces a interference fringe on accountof the primer layer. For that reason, adjusting the refractive index ispreferable by blending a fine particle of a metal oxide with the primerlayer.

Illustrative examples of these metal oxide fine particles include oneoxide fine particle or two or more oxide fine particles or one compositefine particle selected from the group consisting of Si, Al, Sn, Sb, Ta,Ce, La, Fe, Zn, W, Zr, In, and Ti. Specifically, examples can includematerials that are made by colloidally dispersing an inorganic oxidefine particle such as SiO₂, SnO₂, Sb₂O₅, CeO₂, ZrO₂, or TiO₂ in adispersing medium such as water, alcohols, or other organic solvents, orinclude materials that are prepared by colloidally dispersing acomposite fine particle composed of two or more inorganic oxidesselected from the group consisting of Si, Al, Sn, Sb, Ta, Ce, La, Fe,Zn, W, Zr, In, and Ti in water, alcohols, or other organic solvents. Theparticle diameter of every particle is suitably from about 1 to about300 mμ.

Furthermore, in order to enhance the dispersion stability in a coatingliquid, a material prepared by treating this fine particle surface withan organic silicon compound or an amine-based compound can be made useof as well.

Organic silicon compounds used on this occasion includesingle-functional silanes, two-functional silanes, three-functionalsilanes, and four-functional silanes. When a silane is treated, ahydrolytic group may be untreated or may be hydrolyzed. In addition,after the treatment, the state in which the hydrolytic groups areallowed to react with the —OH groups of the fine particles ispreferable, but a state in which some even remain unreacted does notcause any problem in stability.

Additionally, amine-based compounds include ammonium, alkyl amines suchas ethylamine, triethyl amine, isopropyl amine, and n-propyl amine;aralkyl amines such as benzyl amine; alicyclic amines such aspiperidine; alkanol amines such as monoethanolamine and triethanolamine.

The amount of addition of these organic silicon compound and aminecompound is preferably within the range of about 1 to about 15% based onthe amount of the fine particle.

The percentage of metal oxide fine particle in the solid matter of aprimer liquid is from 0 to 65% by weight, particularly desirably 55% byweight or less. When the percentage exceeds 65% by weight, the primerlayer becomes whitish, which worsens the appearance in some cases.

A method for forming a primer layer on a plastic lens base materialinvolves, for example, placing, as appropriate, a metal oxide fineparticle in an aqueous solution containing water borne acryl/urethaneresin, and as required diluting the resulting material with a solvent toprepare a primer liquid to be used. The solvents for the use includesolvents such as alcohols, esters, ketones, ethers, and aromaticcompounds. In addition, a variety of additives that are conventionallywell known such as a leveling agent can be included. The primer liquidthus prepared is applied to a plastic lens base material by means suchas spin coating or dipping, and after the drying, a curing method can becarried out.

On the other hand, examples of polyester-based thermoplastic elastomerscan be found in Japanese Patent Laid-open No. 2000-144048.

A polyester-based thermoplastic elastomer includes a multi-blockcopolymer in which the hard segment uses a polyester and in which thesoft segment uses a polyether or a polyester. The weight ratio of thehard segment (H) to the soft segment (S) is from H/S=30:70 to 90:10,desirably from 40:60 to 80:20.

A polyester as a component of the hard segment composition basicallyincludes a dicarboxylic acid and a low molecular weight glycol.dicarboxylic acids include aromatic dicarboxylic acids such asterephthalic acid, isophthalic acid, phthalic acid, and 2,6-naphthalenedicarboxylic acid; straight chain saturated aliphatic dicarboxylic acidshaving a carbon number of 4 to 20 such as succinic acid, adipic acid,azelaic acid, decamethylene dicarboxylic acid, and octadecanedicarboxylic acid; aliphatic oxocarboxylic acids such asε-hydroxycaproic acid; dimer acids (dibasic acids prepared by dimerpolymerizing an aliphatic monocarboxylic acid having a double bond) andthese ester-forming derivatives. Even of these, terephthalic acid and2,6-naphthalene dicarboxylic acid are desirably used.

In addition, low molecular weight glycols include aliphatic glycols suchas ethylene glycol, trimethylene glycol, 1,4-butanediol,1,5-pentanediol, 1,6-hexanediol, neopentyl glycol; aliphatic glycolssuch as 1,6-cyclohexanedimethanol; and these ester-forming derivatives.Of these, ethylene glycol and 1,4-butanediol are desirably used.

A polyester as a component of the soft segment composition includes adicarboxylic acid and a long chain glycol, and dicarboxylic acidsinclude the above-mentioned species. Long chain glycols includepoly(1,2-butadiene glycol), poly(1,4-butadiene glycol), and the hydrogenadditives thereof. Moreover, ε-caprolactone (C6), enantholactone (C7),and caprolirolactone (C8) are useful as polyester components as well. Ofthese, ε-caprolactone is desirably used.

Polyethers as components of the soft segment composition includepoly(alkylene oxide) glycols such as poly(ethylene oxide) glycol,poly(1,2-propyleneoxide) glycol, poly(1,3-propyleneoxide) glycol, andpoly(tetramethyleneoxide) glycol. Of these, poly(tetramethyleneoxide)glycol is desirably used.

A method for producing a polyester-based thermoplastic elastomerinvolves, for example, heating a lower alkyl ester of a dicarboxylicacid, an aliphatic long chain glycol, and an excessive low molecularweight glycol in the presence of tetrabutyltitanate or the like as acatalyst at a temperature of 150 to 200° C. to carry out an esterexchange reaction, first forming a low polymer and further heating andagitating this low polymer in a high vacuum at 220 to 280° C. to conductpolycondensation and to obtain the polyester-based thermoplasticelastomer. The aforementioned low polymer can also be obtained by adirect esterification reaction of a dicarboxylic acid, a long chainglycol, and a low molecular weight glycol.

A polyester-based thermoplastic elastomer can be mixed with otherpolymers for use, for example, arbitrarily with normal ester-based resin(PBT, PET, or the like), amide-based resin, and further amide-basedthermoplastic elastomers. Normally, the content of polyester-basedthermoplastic elastomer based on all the polymers is less than 50%,desirably below 30%.

A polyester-based thermoplastic elastomer can be changed to prepare aprimer composition of a solution type. However, in terms ofprocessability and environmental protection, a primer composition of anaqueous emulsion is desirable for use. Making an emulsion water-solublecan be performed by a well-known process. Specifically, the forcingemulsifying process is desirable in which a high mechanical shear isapplied to a polymer to forcibly be emulsified in the presence of asurfactant (external emulsifying agent).

A primer composition is desirable to contain a metal oxide fine particle(including a composite fine particle) for the purpose of adjusting therefractive index and improving the strength, and the like. For the metaloxide fine particle, species illustrated in the above-described waterborne acryl/urethane resin are similarly usable.

The primer liquid thus prepared is applied to a plastic lens basematerial by means such as spin coating or dipping, and after the drying,a curing method can be carried out.

The film thickness of a primer containing as the main component waterborne acryl/urethane resin or a polyester-based thermoplastic elastomeris from 0.01 to 50 μm, particularly preferably from 0.1 to 30 μm. Whenthe primer layer is too thin, the hard coat layer of a colorable type isdecreased in improvement in coloring properties and in an improvingeffect of shock impact resistance. Conversely, if the thickness is toolarge, the smoothness of the surface is lost or the optical distortionoccurs in some cases.

Next, the hard coat layer will be set forth. The hard coat layer in aplastic lens of the present invention is formed from a hard coatcomposition containing Components (A), (B), (C), and (D) below.

Component (A) includes an inorganic fine particle having a particlediameter of 1 to 100 millimicrons; Component (B) includes an organicsilicon compound expressed in terms of Formula (1):

(wherein R¹ is an organic group containing a reaction group capable ofbeing polymerized, R² is a hydrocarbon group having a carbon number of 1to 6, X is a hydrolyzable group, and n is 0 or 1); Component (C)includes a multi-functional epoxy compound; and (D) includes a curingcatalyst.

Illustrative examples of Component (A) of inorganic fine particlesinclude one oxide fine particle or two or more oxide fine particles orone composite fine particle of metals selected from the group of Si, Al,Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti. Specifically, examplescan include materials that are made by colloidally dispersing aninorganic oxide fine particle such as SiO₂, SnO₂, Sb₂O₅, CeO₂, ZrO₂, orTiO₂ in a dispersing medium such as water, alcohols, or other organicsolvents, or include materials that are prepared by colloidallydispersing a composite fine particle composed of two or more inorganicoxides selected from the group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W,Zr, In, and Ti in water, alcohols, or other organic solvents. For anobject of the present invention, the average particle diameter of 1 to100 millimicrons is used, preferably a particle with a diameter of 5 to30 millimicrons is desirable. Furthermore, in order to enhance thedispersion stability in a coating liquid, as described above, a materialprepared by treating this fine particle surface with an organic siliconcompound or an amine-based compound can be made use of as well.

The kind and the amount of blending of an inorganic fine particle aredetermined by a desired hardness and reflective index, etc. The amountof blending of the aforementioned inorganic fine particle is from 5 to80% by weight, particularly desirably from 10 to 50% by weight, relativeto the solid matter of the hard coat composition. When the amount ofblending of the aforementioned inorganic fine particle is too small, theadhesion properties with the anti-reflection coating becomeinsufficient, or the abrasion resistance of the film is sometimesinsufficient. In addition, too large an amount of blending of theaforementioned inorganic fine particle causes cracks in the film andalso causes the coloring properties to be insufficient in some cases.

An organic silicon compound of Component (B) serves as a vehiclecomponent. In Formula (1) above, R¹ is an organic group containing areaction group capable of being polymerized and the reaction groupscapable of being polymerized include, for example, a vinyl group, anallyl group, an acryl group, a methacrylic group, an epoxy group, amercapto group, a cyano group, an isocyano group, and an amino group. R²is a hydrocarbon group having a carbon number of 1 to 6, and theexamples include a methyl group, an ethyl group, a butyl group, a vinylgroup, and a phenyl group. Additionally, X is a hydrolyzable functionalgroup, and the examples include alkoxy groups such as a methoxy group,an ethoxy group, and a methoxyethoxy group; halogen groups such as achloro group and a bromo group; and an acyloxy group.

Organic silicon compounds of Component (B) include, for example,vinyltrialkoxysilane, vinyltrichlorosilane,vinyltri(β-methoxy-ethoxy)silane, allyltrialkoxysilane,acryloxypropyltrialkoxysilane, methacryloxypropyltrialkoxysilane,methacryloxypropyldialkoxymethylsilane,γ-glycidoxypropyltrialkoxysilane,β-(3,4-epoxycyclohexyl)-ethyltrialkoxysilane,mercaptopropyltrialkoxysilane, γ-aminopropyltrialkoxysilane, andN-β(aminoethyl)-γ-aminopropylmethyldialkoxysilane. These compounds ofComponent (B) may be used in a mixture of two or more species. Moreover,the use after hydrolysis is more effective in use.

The amount of use of Component (B) is from 10 to 70% by weight,particularly desirably from 20 to 60% by weight, based on the solidmatter of a hard coat composition. Too small an amount of blending ofComponent (B) causes the adhesion properties with the reflectivepreventing film to be apt to be insufficient in some cases. On the otherhand, too large an amount of blending of Component (B) causes the curedfilm to be sometimes cracked.

A multi-functional epoxy compound of Component (C) serves as a coloringcomponent for the hard coat layer. A multi-functional epoxy compound isspecifically excellent in adhesion properties for water borneacryl-urethane resin and a polyester-based thermoplastic elastomer ofthe above-described primer layer. Moreover, the presence of a primerlayer is much higher in coloring properties than the case where a hardcoat layer of colorable type is in a single layer on a plastic lens basematerial. For that reason, placing a primer layer enables reduction ofthe amount of blending of a multi-functional epoxy compound in a hardcoat of colorable type and ensures sufficient coloring properties,thereby leading to obtaining a plastic lens having further hardness andthus the improvement in scratch resistance. In addition, amulti-functional epoxy compound can improve the water resistance and thehot water resistance of a hard coat layer, and even though the hard coatlayer is soaked in a hot coloring solution during coloring for a longwhile, the occurrence of cracks can be effectively suppressed. Moreover,a hard coat layer containing a multi-functional epoxy compound canimprove the shock impact resistance of the plastic lens.

Multi-functional epoxy compounds are widely commercialized foradhesives, cast material, etc. and include, for example,polyolefin-based epoxy resin synthesized by the peroxidation process;alicyclic epoxy resin such as polyglycidyl esters obtained by reactionsbetween cyclopentadieneoxide, cyclohexeneoxide, or hexahydrophthalicacid, and epichlorohydrin; polyglycidyl ether obtained by reactionsbetween polyols and epichlorohydrin, the polyols include polyphenolssuch as bisphenol A, catechol, and resorcinol, polyalcohols such as(poly)ethylene glycol, (poly)propylene glycol, neopentyl glycol,glycerin, trimethylol propane, pentaerythritol, diglycerol, andsorbitol; epoxidized vegetable oil, epoxy novolac obtained from areaction between novolac type phenol resin and epichlorohydrin; epoxyresin obtained from a reaction of phenolphthalein and epichlorohydrin;copolymers obtained from glycidylmethacrylate, and amethylmethacrylateacrylic monomer, styrene, etc. and furtherepoxyacrylates obtained from a glycidyl group ring-opening reaction ofthe above-described epoxy compounds and methacrylic acid containing amonocarboxylic acid.

Examples of multi-functional epoxy compounds include aliphatic epoxycompounds such as 1,6-hexanediol glycidyl ether, ethylene glycoldiglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycoldiglycidyl ether, tetraethylene glycol diglycidyl ether, nonaethyleneglycol diglycidyl ether, propylene glycol diglycidyl ether, dipropyleneglycol diglycidyl ether, tripropylene glycol diglycidyl ether,tetrapropylene glycol diglycidyl ether, nonapropylene glycol diglycidylether, neopentyl glycol diglycidyl ether, diglycidyl ether of hydroxypivalic acid neopentyl glycol ester, trimethylol propane diglycidylether, trimethylol propane diglycidyl ether, trimethylol propanetriglycidyl ether, glycerol diglycidyl ether, glycerol triglycidylether, diglycerol diglycidyl ether, diglycerol triglycidyl ether,diglycerol tetraglycidyl ether, pentaerythritol diglycidyl ether,pentaerythritol triglycidyl ether, pentaerythritol tetraglycidyl ether,dipentaerythritol tetraglycidyl ether, sorbitol tetraglycidyl ether,diglycidyl ether of tris(2-hydroxyethyl)isocyanurate, and triglycidylether of tris(2-hydroxyethyl)isocyanurate; alicyclic epoxy compoundssuch as isophorondiol diglycidyl ether andbis-2,2-hydroxycyclohexylpropane diglycidyl ether; aromatic epoxycompounds such as resorcin diglycidyl ether, bisphenol A diglycidylether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether,diglycidyl orthophthalate, phenol novolac polyglycidyl ether, and cresolnovolac polyglycidyl ether.

The presence of a hydroxyl group in the molecule of a multi-functionalepoxy compound of Component (C) in the present invention improvesadhesion properties with the primer layer and coloring properties. Assuch, a multi-functional epoxy compound preferably contains a pluralityof epoxy groups and one or more hydroxyl groups in the molecule. Forexample, the aforementioned species that are preferably usable includeneopentyl glycol diglycidyl ether, trimethylol propane diglycidyl ether,glycerol diglycidyl ether, diglycerol triglycidyl ether, pentaerythritoldiglycidyl ether, pentaerythritol triglycidyl ether, diglycidyl ether oftris(2-hydroxyethyl)isocyanurate, phenol novolac polyglycidyl ether, andcresol novolac polyglycidyl ether. Referring to the present invention,multi-functional epoxy compounds, each containing a plurality of epoxygroups and one or more hydroxyl groups in the molecule, are used singlyor in a combination of two or more species, and further theaforementioned compounds can be used in combination with amulti-functional epoxy compound without a hydroxyl group in themolecule.

The amount of blending of a multi-functional epoxy compound of Component(C) is from 5 to 40% by weight relative to the solid matter in a hardcoat composition when a hard coat layer is directly applied to a plasticlens base material, whereas in the case of forming the hard coat via aprimer layer, the amount of blending of the multi-functional epoxycompound can be reduced to from 0.1 to 25% by weight, preferably from0.5 to 20% by weight on account of the coloring properties beingimproved by the presence of the primer layer. Too small an amount ofblending of the aforementioned compound renders the water resistance ofthe film to be insufficient in some cases; on the other hand, too largean amount of blending of the aforementioned compound causes the adhesionproperties with the anti-reflection coating to tend to be insufficientin some cases.

A curing catalyst of Component (D) is added as the curing catalyst for asilanol or an epoxy compound, and preferable species include perchloricacids such as perchloric acid, ammonium perchlorate, and magnesiumperchlorate; acetylacetonates containing as the central metal atom suchas Cu(II), Zn(II), Co(II), Ni(II), Be(II), Ce(III), Ta(III), Ti(III),Mn(III), La(III), Cr(III), V(III), Co(III), Fe(III), Al(III), Ce(IV),Zr(IV), V(IV), etc.; amino acids such as amines and glycine; Lewisacids; and organic acid metal salts. Of these, compositions of thepresent invention are preferably magnesium perchlorate, acetylacetonatesof Al(III), and Fe(III) due to curing conditions, a pot life, etc. Theamount of the aforementioned curing catalyst desirably ranges from 0.01to 5.0% by weight the concentration of the solid matter.

A composition for a hard coat thus obtained can be used, as appropriate,to be diluted in a solvent. Solvents for use include alcohols, esters,ketones, ethers, and aromatic compounds.

Moreover, according to a hard coat composition of the present invention,in addition to the aforementioned components, the application propertiesand film performance subsequent to curing of the hard coat liquid can beimproved, as required, as well by adding a small amount of surfactant,antistatic additive, ultraviolet absorbing agent, antioxidant,dispersing, oil-soluble and fluorescent dyes and pigments, photochromiccompounds, and light and heat resistant stabilizers such as hinderedamine- and hindered phenol-based species, or the like. In particular,addition of one species or two or more species selected from the groupof ultraviolet absorbing agents, antioxidants, and light and heatresistant stabilizers such as hindered amine- and hindered phenol-basedspecies can impart excellent weather resistant properties to a hard coatfilm.

Applying and curing processes of a hard coat composition include thedipping process, the spinner process, the spraying process, and theflowing process, which involve applying a hard coat composition to aplastic lens base material on which a primer layer is formed, and thenheat drying the resulting material at a temperature of 40 to 200° C. forhours, and thereby can form a film.

The film thickness of a hard coat layer ranges from 0.05 to 30 μm,particularly preferably from 0.1 to 20 μm. When the film is too thin,the fundamental performance is not performed in some case. On the otherhand, if the film is too thick, optical distortion is sometimesgenerated.

A plastic lens of the present invention can form an anti-reflectioncoating on the hard coat layer.

An anti-reflection coating is composed of a single layer or amulti-layer of an inorganic film, or an organic film. Materials of theinorganic film include inorganic materials such as SiO₂, SiO, ZrO₂,TiO₂, TiO, Ti₂O₃, Ti₂O₅, Al₂O₃, Ta₂O₅, CeO₂, MgO, Y₂O₃, SnO₂, MgF₂, andWO₃, and these can be used solely or in a combination of two or morespecies. In the case of a plastic lens, SiO₂, ZrO₂, TiO₂, Ta₂O₅ arepreferable that are capable of being vacuum evaporated at a lowtemperature. In addition, a multi-layer film composition preferably hasSiO₂ as the outermost layer.

Usable methods for forming an inorganic film include, for example, thevacuum evaporating method, the ion plating method, the spatteringmethod, the CVD method, and a method that entails depositing a film in asaturated solution by chemical reaction. The vacuum evaporating methodalso makes use of the ion beam assisting method that simultaneously anion beam is irradiated during evaporation.

The material of an organic film is selected considering the refractiveindex of a plastic lens and the hard coat layer. In addition to thevacuum evaporation, applying methods excellent in mass production suchas the spin coating method and dip coating method can be used for makinga film.

Additionally, when forming an anti-reflection coating, the surface ofthe hard coat layer is desired for being treated. Examples of thissurface treatment include acid treatment, alkali treatment, ultravioletirradiation treatment, plasma treatment by high-frequency electricaldischarge in an argon or oxygen atmosphere, and ion beam irradiationtreatment with argon, oxygen, nitrogen, or the like.

Furthermore, in order to make the surface of the anti-reflection coatingdifficult to contaminate, or easy to wipe stains, the use of a fluorinesilane-containing compound bearing a perfluoroalkyl group or the likeenables the formation of a water repellent film on the anti-reflectioncoating.

Hereinafter, detailed descriptions will be set forth using examples.

EXAMPLE 1

(1) Formation of a Primer Layer

A commercially available water-based polyester “A-160P” (product ofTakamatsu Oil & Fat Co., Ltd.; concentration of solid matter, 25%) of186 Grams, methanol of 257 g, water of 15 g, and butylcellosolve of 37 gwere admixed, then to the resultant mixture were addedγ-glycidoxypropyltrimethoxysilane of 5 g and a silicone-based surfactant(product of Nippon Unicar Co., Ltd., trade name “L-7604”) of 0.1 g, andthe material was stirred for three hours. This primer composition wasapplied to a plastic lens base material of SEIKO Super Sovereign (tradename; product of Seiko Epson Corporation; refractive index, 1.67) by theimmersing method (raising speed, 15 cm/min). The applied base materiallens was subjected to heat curing treatment at 100° C. for 20 minutes toform a primer layer having a thickness of 1.0 μm on the base material.

(2) Formation of a Hard Coat Layer

Butylcellosolve of 73 g, methanol of 148 g, andγ-glycidoxypropyltrimethoxysilane of 57 g were mixed. To this mixturesolution was dropped a 0.1N aqueous hydrochloric acid solution of 18 gwith agitating. The resulting mixture was stirred for another threehours and then was aged during one whole day and night. To this solutionwere added a methanol-dispersed SiO₂ fine particle sol (product ofCatalyst & Chemicals Ind. Co., Ltd.; trade name “Oskal 1132”;concentration of solid matter, 30%) of 146 g, a diglycerol polyglycidylether (product of Nagase ChemteX Corporation.; trade name “DenacolEX-421”) of 50 g, magnesium perchlorate of 3 g, a silicone-basedsurfactant (product of Nippon Unicar Co., Ltd., trade name “L-7001”) of0.16 g, and a phenol-based antioxidant (product of Kawaguchi ChemicalIndustry Co., Ltd., trade name “Antage Crystal”) of 0.6 g, and theresulting mixture was mixed for four hours, and then this mixture wasaged during one whole day and night to yield a applying solution. Thishard coat composition was applied to the plastic lens base material onwhich the primer layer obtained in (1) was formed, by means of theimmersing method (raising speed, 30 cm/min). The base material lens thusapplied was subjected to heat curing treatment at 125° C. for threehours to thereby form a hard coat layer having a thickness of 2.5 μm onthe base material.

EXAMPLE 2

On the plastic lens obtained in Example 1 were formed an anti-reflectioncoating and a water repellent film, composed of inorganic material, bythe following method.

(1) Formation of an Anti-Reflection Coating and a Water Repellent Film

On a plastic lens was constructed an anti-reflection multi-layer coatingthat includes seven layers made by laminating an SiO₂ layer and a TiO₂layer alternately in the order from the base plate side. Construction ofthe films of the anti-reflection coating SiO₂ layer was carried out bythe vacuum evaporating method (degree of vacuum, 5.0×10⁻⁴ Pa). Makingthe films of the TiO₂ layer was conducted by the ion assist evaporatingmethod (degree of vacuum, 4.0×10⁻³ Pa). The ion assist conditions whenmaking the films of the TiO₂ layer by the ion assist evaporating methodincludes an acceleration voltage of 520 V, an acceleration current valueof 270 mA, and a degree of vacuum of 4.0×10⁻³ Pa, which was made kept byintroducing oxygen. An anti-reflection coating was constructed bylaminating the layers one by one in the following order: the first layerfrom the base material side is an SiO₂ layer having an optical thicknessof 0.083 λ, the second layer is a TiO₂ layer having an optical thicknessof 0.07 λ, the third layer is an SiO₂ layer having an optical thicknessof 0.10 λ, the fourth layer is a TiO₂ layer having an optical thicknessof 0.18 λ, the fifth layer is an SiO₂ layer having an optical thicknessof 0.065 λ, the sixth layer is a TiO₂ layer having an optical thicknessof 0.14 λ, and the seventh layer is an SiO₂ layer having an opticalthickness of 0.26 λ. The design wavelength A was set to be 520 nm. Thereflection-interference colors of the multi-layer film thus obtainedturned green and the total light transmittance was 99%.

Furthermore, a water repellent film composed of a fluorine-containingsilane compound was formed on the anti-reflection coating by a vacuumevaporating method.

EXAMPLE 3

(1) Formation of a Primer Layer

A primer layer was formed by the method as in the case of Example 1.

(2) Formation of a Hard Coat Layer

Butylcellosolve of 68 g, methanol of 139 g, andγ-glycidoxypropyltrimethoxysilane of 61 g were mixed. To this mixturesolution was dropped a 0.1N aqueous hydrochloric acid solution of 17 gwith agitating. The resulting mixture was stirred for another threehours and then was aged during one whole day and night. To this solutionwere added a methanol-dispersed SiO₂ fine particle sol (product ofCatalyst & Chemicals Ind. Co., Ltd.; trade name “Oskal 1132”;concentration of solid matter, 30%) of 181 g, a diglycerol polyglycidylether (product of Nagase ChemteX Corporation.; trade name “DenacolEX-421”) of 26 g, magnesium perchlorate of 3 g, a silicone-basedsurfactant (product of Nippon Unicar Co., Ltd., trade name “L-7001”) of0.15 g, a silicone-based surfactant (product of Nippon Unicar Co., Ltd.,trade name “L-7604”) of 0.05 g, a phenol-based antioxidant (product ofKawaguchi Chemical Industry Co., Ltd., trade name “Antage Crystal”) of0.6 g, and a benzotriazol-based ultraviolet absorbing agent (product ofCiba Specialty Chemicals Co., Ltd., trade name “TINUVIN 213) of 3.7 g.The resulting mixture was mixed for four hours, and then this mixturewas aged during one whole day and night to yield an applying solution.This hard coat composition was applied to the plastic lens base materialon which the primer layer obtained in (1) was formed, by means of theimmersing method (raising speed, 35 cm/min). The base material lens thusapplied was subjected to heat curing treatment at 125° C. for threehours to thereby form a hard coat layer having a thickness of 2.5 μm onthe base material.

EXAMPLE 4

On the plastic lens obtained in Example 3 were formed an anti-reflectioncoating and a water repellent film by the method as in Example 2.

EXAMPLE 5

(1) Formation of a Primer Layer

A primer layer was formed by the method as in the case of Example 1.

(2) Formation of a Hard Coat Layer

A hard coat layer was formed all by the method as in Example 3, with theexception that a diglycerol polyglycidyl ether (product of NagaseChemteX Corporation.; trade name “Denacol EX-421”) was changed into1,6-hexadiol diglycidyl ether (product of Nagase ChemteX Corporation.;trade name “Denacol EX-212”).

EXAMPLE 6

(1) Formation of a Primer Layer

A commercially available aqueous emulsion polyurethane “Neosticker 700”(product of Nicca Chemical Co., Ltd., concentration of solid matter,37%; acryl-modified polyurethane) of 126 Grams, methanol of 258 g, waterof 74 g, and butylcellosolve of 37 g were admixed, and then to theresultant mixture were added 5 g of γ-glycidoxypropyltrimethoxysilaneand a silicone-based surfactant (product of Nippon Unicar Co., Ltd.,trade name “L-7604”) of 0.1 g and the material was stirred for threehours. This primer composition was applied to a plastic lens basematerial of SEIKO Super Sovereign (trade name; product of Seiko EpsonCorporation; refractive index, 1.67) by the immersing method (raisingspeed, 15 cm/min). The applied base material lens was subjected to heatcuring treatment at 100° C. for 20 minutes to form a primer layer havinga thickness of 1.0 μm on the base material.

(2) Formation of a Hard Coat Layer

A hard coat layer was formed by the method as in Example 3.

EXAMPLE 7

On the plastic lens obtained in Example 6 were formed an anti-reflectioncoating and a water repellent film by the method as in Example 2.

EXAMPLE 8

(1) Formation of a Primer Layer

A primer layer was formed all by the method as in Example 6, with theexception that the plastic lens base material was changed into a plasticlens base material of SEIKO Super Luscious (trade name; product of SeikoEpson Corporation; refractive index, 1.60).

(2) Formation of a Hard Coat Layer

A hard coat layer was formed all by the method as in Example 3, with theexception that the diglycerol polyglycidyl ether (product of NagaseChemteX Corporation.; trade name “Denacol EX-421”) was changed into aglycerol polyglycidyl ether (product of Nagase ChemteX Corporation.;trade name “Denacol EX-313”).

(3) Formation of an Anti-Reflection Coating and a Water Repellent Film

The plastic lens obtained in (2) was subjected to plasma treatment(argon plasma 400W×60 sec), and then an anti-reflection multi-layercoating that includes five layers made by laminating an SiO₂ layer and aZrO₂ layer alternately in the order from the base plate side wasconstructed. The optical thickness of each layer was formed such thatthe first SiO₂ layer, the next ZrO₂ layer and the SiO₂ layer, the filmlayers of which are equivalent, the next ZrO₂ layer and the uppermostlayer of the SiO₂ layer are each λ/4. In addition, the design wavelengthλ was set to be 520 nm. The reflection-interference colors of themulti-layer film thus obtained turned green and the total lighttransmittance was 98%.

Furthermore, a water repellant film composed of a fluorine-containingsilane compound was formed on the anti-reflection coating by a vacuumevaporating method.

EXAMPLE 9

(1) Formation of a Primer Layer

A primer layer was formed all by the method as in Example 6, with theexception that the plastic lens base material was changed into a plasticlens base material of SEIKO Prestige (trade name; product of Seiko EpsonCorporation; refractive index, 1.74).

(2) Formation of a Hard Coat Layer

A hard coat layer was formed by the method as in Example 3.

(3) Formation of an Anti-Reflection Coating and a Water Repellent Film

An anti-reflection coating and a water repellent film were formed by themethod as in Example 2.

EXAMPLE 10

(1) Formation of a Primer Layer

A primer layer was formed all by the method as in Example 1, with theexception that the plastic lens base material was changed into a plasticlens base material of SEIKO Super Luscious (trade name; product of SeikoEpson Corporation; refractive index, 1.60).

(2) Formation of a Hard Coat Layer

A hard coat layer was formed by the method as in Example 3.

(3) Formation of an Anti-Reflection Coating and a Water Repellent Film

An anti-reflection coating and a water repellent film were formed by themethod as in Example 2.

EXAMPLE 11

(1) Formation of a Primer Layer

A primer layer was formed all by the method as in Example 1, with theexception that the plastic lens base material was changed into a plasticlens base material of SEIKO Prestige (trade name; product of Seiko EpsonCorporation; refractive index, 1.74).

(2) Formation of a Hard Coat Layer

A hard coat layer was formed all by the method as in Example 3, with theexception that the diglycerol polyglycidyl ether (product of NagaseChemteX Corporation.; trade name “Denacol EX-421”) was changed into aglycerol polyglycidyl ether (product of Nagase ChemteX Corporation.;trade name “Denacol EX-313”).

(3) Formation of an Anti-Reflection Coating and a Water Repellent Film

An anti-reflection coating and a water repellent film were formed by themethod as in Example 8.

COMPARATIVE EXAMPLE 1

A plastic lens was formed all by the method as in Example 3, except thata primer layer was not formed, and except that on a plastic lens basematerial was formed a hard coat layer in a single layer.

COMPARATIVE EXAMPLE 2

On the plastic lens obtained in Comparative Example 1 were formed ananti-reflection coating, composed of an inorganic material, and a waterrepellent film by means of the method as in Example 2.

COMPARATIVE EXAMPLE 3

(1) Formation of a Primer Layer

A primer layer was formed by the method as in the case of Example 1.

(2) Formation of a Hard Coat Layer

A hard coat layer was formed all by the method as in the case of Example3, except that a diglycerol polyglycidyl ether (product of NagaseChemteX Corporation.; trade name “Denacol EX-421”) was changed into ahydrolysate of N,N-bis[(methyldimethoxysilyl)propyl]amine.

COMPARATIVE EXAMPLE 4

(1) Formation of a Primer Layer

A primer layer was formed by the method as in the case of Example 1.

(2) Formation of a Hard Coat Layer

A hard coat layer was formed all by the method as in the case of Example3, except that a diglycerol polyglycidyl ether (product of NagaseChemteX Corporation.; trade name “Denacol EX-421”) was not added.

COMPARATIVE EXAMPLE 5

On the plastic lens obtained in Comparative Example 4 were formed ananti-reflection coating, composed of an inorganic material, and a waterrepellent film by means of the method as in Example 2.

Plastic lens obtained by these Examples and Comparative Examples wereevaluated in the following.

(a) Appearance, a lens was observed for whitishness, cracks, whitening,etc. with transmitted light and reflected light using a fluorescent lampagainst a black background in a dark box.

(b) Scratch resistance, a lens was visually observed for the scratchedextent after the sample was subjected to the application of a load of 1kg with Bonstar #0000 steel wool (product of Nihon Steel Wool Co., Ltd.)and after the sample surface was rubbed 10 times back and forth.

(c) Weather resistance, a lens that has no changes in the surfaceconditions was considered good after the sample was exposed to a xenonlamp of a sunshine weather meter for 250 hours.

(d) Humidity resistance, a lens that has no changes in the surfaceconditions was considered good after the sample was allowed to stand for10 days in 60° C.×99% environments.

(e) Adhesion properties of a surface-treated layer, a lens on which thetests (c) and (d) were conducted was carried out for adhesion propertiesbetween a lens base material and the surface-treated layer (the hardcoat layer and the anti-reflection coating) by means of cross cut tapetesting in accordance with JIS D-0202. In other words, breaks at 1-mmintervals were made on the base material surface with a knife to form100 one-square-mm squares. Next, cellophane adhesive tape (product ofNichiban Co., Ltd.; trade name “Cellotape” [registered trademark]) wasstrongly pressed thereagainst, and then the tape was rapidly pulled offin the vertical direction relative to the base material surface.Thereafter, the base material surface was visually observed regardingthe squares on which a coated layer remained as an index of adhesionproperties.

(f) Shock impact resistance, a hard ball of 16.3 g was naturally fallenat the center of the convex of a lens from a height of 127 cm to checkthe break of the lens. A lens without breaks or cracks was marked with◯. In addition, lenses used in this testing were all 1.1 mm thick at thecenter of the lens. Furthermore, when the weight of the hard ball wasmade twice, a lens that did not have breaks or cracks was marked with ⊚.

(g) Coloring properties, a plastic lens having the outermost surfacelayer thereof being a hard coat layer was tested. The lens was madeimmersed in a dispersed dye solution bath of 94° C. for 10 minutes todetermine the luminous transmittance with a spectrophotometer. A lenshaving a luminous transmittance of 30% or less was marked with ⊚; a lenshaving a luminous transmittance of 50% or less was marked with ◯; a lenshaving a luminous transmittance of 70% or less was marked with Δ; and alens having a luminous transmittance of exceeding 70% was marked with X.

(h) Hot water resistance, a plastic lens was soaked in hot water of 90°C. for 60 minutes to visually observe the occurrence of cracks,whitening, etc.

A list of the compositions and the components thereof of the treatedlayers of Examples and Comparative Examples is tabulated in Table 1, andthe test results are shown in Table 2. TABLE 1 Amount of blending ofcoloring Hard Anti- component to solid coat reflection matter Primerlayer layer coating Coloring component (% by weight) Example 1Polyester-based Present Absent Diglycerol polyglycidyl ether About 32thermoplastic elastomer Example 2 Polyester-based Present PresentDiglycerol polyglycidyl ether About 32 thermoplastic elastomer Example 3Polyester-based Present Absent Diglycerol polyglycidyl ether About 18thermoplastic elastomer Example 4 Polyester-based Present PresentDiglycerol polyglycidyl ether About 18 thermoplastic elastomer Example 5Polyester-based Present Absent 1,6-Hexanediol diglycidyl ether About 18thermoplastic elastomer Example 6 Water borne Present Absent Diglycerolpolyglycidyl ether About 18 acryl/urethane resin Example 7 Water bornePresent Present Diglycerol polyglycidyl ether About 18 acryl/urethaneresin Example 8 Water borne Present Present Glycerol polyglycidyl etherAbout 18 acryl/urethane resin Example 9 Water borne Present PresentDiglycerol polyglycidyl ether About 18 acryl/urethane resin Example 10Polyester-based Present Present Diglycerol polyglycidyl ether About 18thermoplastic elastomer Example 11 Polyester-based Present PresentGlycerol polyglycidyl ether About 18 thermoplastic elastomer ComparativeAbsent Present Absent Diglycerol polyglycidyl ether About 18 Example 1Comparative Absent Present Present Diglycerol polyglycidyl ether About18 Example 2 Comparative Polyester-based Present Absent Hydrolysate ofN,N-bis About 18 Example 3 thermoplastic elastomer[(methyldimethoxysilyl)propyl]amine Comparative Polyester-based PresentAbsent Absent — Example 4 thermoplastic elastomer ComparativePolyester-based Present Present Absent — Example 5 thermoplasticelastomer

TABLE 2 Scratch Weather Humidity Adhesion Shock impact Coloring Hotwater Appearance resistance resistance resistance properties resistanceproperties resistance Example 1 ⊚ Δ ◯ ⊚ ⊚ ⊚ ⊚ ⊚ Example 2 ⊚ ◯ ⊚ ⊚ Δ ⊚ —⊚ Example 3 ⊚ ◯ ◯ ⊚ ⊚ ⊚ ◯ ◯ Example 4 ⊚ ⊚ ⊚ ⊚ ⊚ ◯ — ◯ Example 5 ⊚ ◯ ◯ ⊚◯ ⊚ Δ ◯ Example 6 ⊚ ◯ ◯ ⊚ ⊚ ⊚ ◯ ◯ Example 7 ⊚ ⊚ ⊚ ⊚ ⊚ ◯ — ◯ Example 8 ⊚⊚ ⊚ ⊚ ⊚ ◯ — ◯ Example 9 ⊚ ⊚ ⊚ ⊚ ⊚ ◯ — ◯ Example 10 ⊚ ⊚ ⊚ ⊚ ⊚ ◯ — ◯Example 11 ⊚ ⊚ ⊚ ⊚ ⊚ ◯ — ◯ Comparative ⊚ ◯ ◯ ⊚ ◯ X Δ ◯ Example 1Comparative ⊚ ⊚ ⊚ ⊚ ◯ X — ◯ Example 2 Comparative ⊚ ◯ ◯ ⊚ X ⊚ ◯ ΔExample 3 Comparative ⊚ ⊚ ◯ ⊚ ◯ ◯ X Δ Example 4 Comparative ⊚ ⊚ ⊚ ⊚ ◯ ◯— Δ Example 5

Because the plastic lens of Example 1 includes a large content (about32% by weight) of a multi-functional epoxy compound in a hard coat, thecoloring properties are good, but the scratch resistance isinsufficient. In addition, in the plastic lens of Example 2, on which ananti-reflection coating is placed on the lens of Example 1, the shockimpact resistance is sufficient. The plastic lens of Example 4, in whichan anti-reflection coating is put on the plastic lens of Example 3, theplastic lens of Example 7, in which an anti-reflection coating is put onthe plastic lens of Example 6, and further the plastic lenses ofExamples 8 to 11, on which an anti-reflection coating each is placed,show decreases in shock impact resistance. This seems to be because theadhesion properties between the hard coat layers and the anti-reflectioncoatings are insufficient. The lens of Example 3 is a lens thatmaintains balance of various permanence properties and coloringproperties. The plastic lens of Example 4, in which an anti-reflectioncoating is put on the plastic lens of Example 3, shows furtherimprovement of scratch resistance and weather resistance. The shockimpact resistance thereof indicates a slight decrease, but a sufficientlevel. The lens of Example 5 is slightly low in coloring properties andadhesion properties due to a structure of the multi-functional epoxycompound not containing a hydroxyl group. The plastic lenses of Examples6 to 11 similarly maintain balance of various properties.

The plastic lenses of Comparative Examples 1 and 2 are low in shockimpact resistance on account of no primer layers. In addition,comparison of the lens of Comparative Example 1 that has a structure inwhich the primer layer is removed from the plastic lens of Example 3with the lens of Example 3 shows that a primer layer has a large effecton coloring properties. The lens of Comparative Example 3 that makes useof a component other than a multi-functional epoxy compound as acoloring component does not have the adhesion properties with the primerlayer. The lens of Comparative Example 4 exhibits almost no coloringproperties because of not using a multi-functional epoxy compound.Furthermore, the lens thereof is also low in hot water properties. Theplastic lens of Comparative Example 5 in which an anti-reflectioncoating is placed on the plastic lens of Comparative Example 4 indicatesthat the hard coat readily suffers from cracks and that the hot waterproperties are low, although an anti-reflection coating is put.

INDUSTRIAL APPLICABILITY

A plastic lens of the present invention can be utilized as a spectaclelens that is excellent in shock impact resistance, is safety, and is foreyesight correction.

In addition, a method for producing a plastic lens of the presentinvention enables production of a spectacle lens that is excellent insuch shock impact resistance, is safety, and is for eyesight correction.

1. A plastic lens, comprising: a plastic lens base material; a primerlayer formed on said plastic lens base material; and a hard coat layerformed on said primer layer, wherein said hard coat layer being formedfrom a hard coat composition, the hard coat composition comprising: (A)an inorganic fine particle having a particle diameter of 1 to 100millimicrons; (B) an organic silicon compound expressed in terms ofFormula (1):

wherein R¹ is an organic group containing a reaction group capable ofbeing polymerized, R² is a hydrocarbon group having a carbon number of 1to 6, X is a hydrolyzable group, and n is 0 or 1; (c) a multi-functionalepoxy compound; and (d) a curing catalyst:
 2. The plastic lens accordingto claim 1, wherein the content of said multi-functional epoxy compoundin the solid matter of said hard coat composition is from 0.1 to 25% byweight.
 3. The plastic lens according to claim 1, wherein said primerlayer comprises water borne acryl/urethane resin as the main component.4. The plastic lens according to claim 1, wherein said primer layercomprises a polyester-based thermoplastic elastomer as the maincomponent.
 5. The plastic lens according to claim 1, wherein saidmulti-functional epoxy compound includes one or more hydroxyl groups inone molecule.
 6. The plastic lens according to claim 1, wherein theplastic lens comprises an anti-reflection coating on said hard coatlayer.
 7. A method for manufacturing a plastic lens, comprising: a stepof forming a primer layer on a plastic lens base material; and a step offorming a hard coat layer on said primer layer from a hard coatcomposition, the hard coat composition comprising: (A) an inorganic fineparticle having a particle diameter of 1 to 100 millimicrons; (B) anorganic silicon compound expressed in terms of Formula (1):

wherein R¹ is an organic group containing a reaction group capable ofbeing polymerized, R² is a hydrocarbon group having a carbon number of 1to 6, X is a hydrolyzable group, and n is 0 or 1; (C) a multi-functionalepoxy compound; and (D) a curing catalyst.